Category Archives: cross dressing phone sex

Sissy boys, it’s about time you got real. And it’s about time you got into the phone sex you really need the most, sissy phone sex with me, a sexy Tranny. I already know the sissy secrets you hide from everyone else. Or you wouldn’t even be calling me. I know how much you fantasize about going all the way and transforming into a shemale. You can’t hide that you wish you could abandon your life as an inadequate man and give in to your dazzling dreams of becoming a real life TGirl. You have what it takes to start, sissies, but you need to begin phone sex transformation sessions where I will be your guide.

Look at my photos, you’re jealous, aren’t you? You want to be a sexy shemale and do nasty phone sex, seduce men, even become a tranny hooker. I’m familiar with the total trans lifestyle and can tell you the exact steps you need to take in order to leave behind your sissy self and become a tranny Goddess. You will need to walk and talk like a girl, look like a girl. Be a girl! By the time I’m done with you, no one will recognize you. You will be mine, a perfect shemale dolly.

I’m very supportive in my approach to transformation, but I expect results. The second you first slipped on a pair of panties has led you to this moment. It’s time to go even further than ever before. Sissy Phone Sex with a sexy shemale Goddess is the sexual destiny for you sissies. Don’t run away from it, my sissy boys! You know you want it and more importantly, need it.

It’s Friday and I have a special night out planned for on our slutty sissy phone sex call. First thing I’m going to do is dress you up like the perfect slut. Stockings and garters with your little panties pulled over the garters. We need to be able to take them off without taking off those stockings. I think a proper slutty sissy needs to have big tits, so let’s get you a bra and stuff it full. A super short mini skirt and a sheer white blouse tied up to show your belly button.

Our first outing for the evening is to my favorite fetish shoe store. No sissy slut outfit would be complete without a pair of 5″ heeled cum fuck me pumps. After I pick out the perfect pair for you, it’s time to pay the man. Oh you forgot your wallet? I think there are other ways of paying up. He leads you to the back room, you get on your knees, and he pulls out his hard fat cock. With my hand on the back of your head, and my other hand on his cock, I tell you to open wide and start sucking like the slut you are. An experienced slut like you should have no problem taking his dick balls deep and sucking every drop of his precious cum. You better not miss any and ruin your outfit or his pants. Don’t make me spank you right here in front of everyone.

A quick stop at the salon for my girl to do your make up and hair. Shiny red cock sucking lipstick, extra long eyelashes, red rosy cheeks, and a long blonde wig complete your look. Perfect for our last stop at my favorite toy store. There is a special event tonight and you are the star. Not only are we going to try all the new dildos and strap-ons, all the guys are going to need someone to take care of their hard cocks. I tie you to a spanking bench, ass up in the air. I pull your head up by your collar so your mouth is available too. When you see them lining up for your sissy slutty boy pussy and your hungry mouth, you can’t wait for the real action to begin.

I really don’t know why I love cross dressing phone sex so much. There’s something so sexy about watching a man eat me out with my lingerie on. I love it so much when a man will get all dressed up for me. The sluttier the better. There’s so many things I love about it, from the way your legs looks in those high heels and stockings, to the way your rock hard cock feels underneath slutty silk panties.

I am getting seriously hot just thinking about it. Not only do I love seeing a man in woman’s lingerie, I love it when he takes control and fucks me in woman’s clothes. There’s something about a dominate man in sexy clothing that really gets my juices flowing, and I can’t help but rub my clit while he tells me what he’s wearing, and how the clothes make him feel. There are so many more reason’s I love cross dressing phone sex. I also love when a man wants to be submissive, and let me take control, and be the man in the situation. Do you want me to lick your asshole over those silk panties, or slide my finger in your ass while I suck your cock? Mmmm, me too.

Cum and have cross dressing phone sex with me. Make me cum while you tell me what you are wearing, and fucking me like a whore that you are. I will make you cum so hard, I can feel you getting hard already, while you’re dialing the phone. You’re a naughty little whore, aren’t you? I want to hear you slide your hand down your panties and rub that hard cock of yours.

A lot of times when guys call for me feminization phone sex, they aren’t expecting the girl on the other end of the line to want to be included in the dressing up part of the fantasy, but I really love getting all dressed up with you and maybe even more than that – doesn’t sharing a big fat cock together sound like so much fun?

But first things first… we need to do what girlfriends do best – we need to go shopping. I’m not saying we should match completely, but I think having matching outfits would be so awesome. What do you think we should wear? Just lingerie, stockings and some heels? Or maybe you want that AND a sexy dress over it. OMG and maybe then we will go get our hair done and stop by the MAC counter for a makeover. Let’s not forget a stop for mani/pedi’s, a girl has to look awesome from head to toe! We’ll make it a girls day, shopping and lunch!

Once we’re back home it’s time to get all dressed up for a night on the town. We’ll be 2 hot bitches ready for whatever the night brings. We go from one bar to a club all with the idea of showing off our skin tight sexy dresses and silky stockinged thigh his. It goes without saying that the sexiest cum fuck me pumnps will be on our feet. Perfect for teasing all the boys (and some girls!)

When those 2 sexy guys offer to buy us drinks I have to invite them over to join us. I whisper in your ear not to be nervous, this will be fun and exciting, just follow my lead. It’s not long before I notice you with your tongue down your new friend’s throat and his hand squeezing your thigh. I can tell how excited you are and so am I! I excuse myself to use the ladies room and just like ladies do, I need you to come with me. Do we invite them back to your place or are we just hot cock teases ready to ditch them right now and just go home together?

How does it end up? For feminization phone sex, call me at 1-888-837-3259 and ask for Erin and once you’re dressed and feeling oh so sexy, we’ll decide what happens next.

If you’ve been dreaming of complete sissy transformation but just didn’t know where to get started, you are totally in the right place. Sissy training phone sex with me will make you feel like the prettiest woman in the word. I’m not just going to tell you to slip into a pair of panties and call it a day. No, we’re going to talk about all of the things it will take to genuinely feel feminine.

Now, I know I said that I’m not JUST going to put you in a pair of panties, but that really is an important part of the sissy training phone sex process. But they shouldn’t be just any panties. You need to pick out a really sexy pair. I think red lace is one of the sexiest thing a woman can wear, so I’d recommend a pair made of that. Getting a matching panty and bra set is probably a really good idea, too. I can’t even explain to you how sexy and feminine it makes me feel to have matching undergarments.

Have you ever used makeup before? I mean, other than red lipstick? I know every sissy has at least tried some red lipstick. But I’m going to teach you all you need to know about which makeup to get and how to apply it. You’re gonna be a pro at putting on your makeup in no time.

But one of the most important parts of sissy training is learning to take a strap on or cock. I know that not all sissies are interested in being fucked by a man, but you do at least need to learn to take a strap on. Do you think you can do it? If not, don’t worry. That’s part of what sissy training is all about – me helping you become a woman in every sense of the word.

What are you waiting for? Call me at 1-888-837-3259 and ask for Erin for the best sissy training phone sex you could ever have!

Do you have a sexy secret that you need a hot girl like me to help you with? You wouldn’t be the first to call me for some hot cross dressing phone sex. There’s nothing I love more than taking a big, strong ‘man’, and making him into my hot, slutty girlfriend.

First we need to do a little bit of landscaping, don’t you think? I know you’ve never shaved your legs before, but I want to see you using that pretty pink razor to make them nice and smooth. Also under your arms. And oh, let’s not forget about . . . down there. *giggles* You want to be a smooth skinned pretty girl, don’t you?

Also, we need to paint your nails. I think a pretty pink color would be very cute on you. Fingers and toes both have to match. I might just even pierce your ears so you can wear some of my pretty earrings. And of course we’ll rub some nice, flowery, scented body lotion all over your smooth, now hairless body.

That’s a good start, but we’ll have to get you some clothes. It will be so fun taking you to the mall, and making you tell the salesgirls that you’re not buying lingerie for me, that you’ll need some that will fit your big man’s body. *giggles* I love watching how red your face gets when the salesgirl’s eyes widen in surprise.

So far you’ve been doing a pretty good job of pretending you’re just doing it because I want you to, but when you feel those silky pink panties sliding up your legs, you’re betrayed by a certain part of you anatomy. *Giggles* No more hiding from Miss Payton, that rapidly hardening cock straining at those delicate panties completely gives you away. You get so hard from being turned into a frilly girl, don’t you? You’ve secretly been dying for some hot cross dressing phone sex.

We have more stores to go to. Once we have your pretty bra and panties, and those lacy thigh high stockings, we still have to find you a sexy short dress and some sky high fuck me heels. I want all the boys to see what a slutty girl I’ve made you into.

We have more to do, though. After all, if you’re going to get all tarted up and go out tonight, you’ll need some makeup won’t you? I could do it myself, but it would be so much more fun to let the department store makeup lady do some special occasion makeup for you. I make you ask her politely, enjoying the embarrassment on your face as she sits you down and starts caking it on. I tell her we want a smoky eye and a red lip, because we want the boys to know you’re open for business. *giggles*

And finally, we have to do something about that hair. If it’s long enough, I’ll curl it for you. I think I’d like to let it hang down your back. Easier to grab that way, later tonight. If it’s not long enough, we’ll just have to get you a sexy wig. Maybe you want to be a redhead, like me?

Now that you’re all dolled up, and everyone can see what a sexy slut you are, we’ll go out to the clubs tonight, and let all the men ogle your pretty, feminine body. It will turn me on so much to watch them grinding against you on the dance floor. Maybe you’ll enjoy exploring your feminine side so much, that later tonight I’ll slide on my strap on, and you will get on your knees like a good slut and suck my big, thick girl cock. *giggles* If you think you want to be a good girl for me, you will love how I make you mine with some hot cross dressing phone sex. So give me a call, and play with Payton.

One of the things I absolutely love about this time of year is that there’s so much beautiful and sexy lingerie available. The only time that’s better, I think, is around Valentine’s Day. And in some ways, Christmastime lingerie is better because you can find it in colors other than pink and red. Not that I dislike pink and red. I just like variety.

When I say this to the guys who call me for sissy and panty boy phone sex, though, a lot of them seem to be surprised by this. It’s like they don’t realize when the best times of the year for lingerie shopping are! But that’s all right because *I* know, and I can teach them.

So if you’re a panty boy who needs some help expanding his wardrobe, then I’m the one you need to talk to. There are so many lovely Christmasy colors to choose from this time of year–red, green, blue, silver, gold, white, and lots more. Not to mention all the different materials. If you don’t own a red velvet thong with white Santa-like fleece stuff around the edges, you have no idea what you’re missing.

So my little panty boy phone sex lovers, I have a solution for you. You can call me, Dru, your favorite phone tranny, and we’ll shop together. And after that…well, who knows what might come next with us both so happy and dolled up so very prettily?

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I know your type. You are a panty boy phone sex slut, aren’t you? You started out sniffing panties you got out of hampers when you were visiting your friends. Sometimes you’d even sniff the panties of the women living in your own house. Then after a while, you started stealing them and taking them home or to your bedroom to jerk off with. Did you wrap them around your dick and jerk with them or did you hold them up to your nose and sniff them while you jerked off? Maybe both?! Did you feel ashamed because of whose panties you were sniffing? I bet you did, but it still didn’t stop you, did it? You shot your load right in them. I wonder how big your stolen panty collection is? You probably have a whole drawer full, don’t you?

And then one day, you decided to slip into a pair and the rest is history! After a while, wearing panties wasn’t enough for you. You started going online and looking at lingerie sites and you finally bit the bullet and made an order. You got stockings, garters, bras, panties, and probably even more. You started putting the lingerie on after work and wearing it to bed at night. You probably even started wearing panties to work instead of boxers. Maybe you’re even wearing stockings and a garter under your pants, too. And it feels so good that you don’t even care if anyone notices, do you?

Do you want to eventually get to the point where you only dress in panties, lingerie and stockings? If you’re looking for a girl to help you with all of your panty boy phone sex fantasies, you should give me a call. I will take you there and help you be exactly who you want to be… a super naughty panty boy slut!

If you’re here, then that must mean you’re curious about shemale phone sex. You’re going to be glad your mind started to wander off in that direction, trust me. Not only am I a gorgeous woman with a dick… I love all different kinds of fetish phone sex fantasies and I love hearing all about what gets you excited, too! I do have a few favorites I want to tell you about…

If you like a sexy woman who wears stockings, you’re in luck. I mean, what’s not to love about that silky feeling as you run your hands up and down my legs? Or maybe you just love the look of them… on me OR on you! I’m up for anything.
Another thing I love are panty boys. I love getting you all dressed up in sexy and frilly panties and helping you tuck your clitty inside them. You’ll prance around and then when I’m ready, I’m going to bend you over, push those panties aside and show you what it’s like to be a girl for real.

Or maybe I’ll put you on your back while I fuck you so you can rub that clitty. And you know what? You’re eventually going to cum and it’ll dribble out into your hand and the thing I want most in the world? To see you eat that cum right off of your hand. I have a huge cum fetish and I love everything to do with it. I’m probably going to shoot my load on your face and feed that to you, too. I want to see you wear every drop of my cum.

When you’re ready for a hot shemale phone sex lover who is into fetishes every bit as much as you are, pick up the phone and call 1-888-837-3259 and ask for Cheyenne today!

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